Mohm Flashcards
(23 cards)
The nitration of quinoline with fuming nitric acid in concentrated (conc.) sul-
furic acid containing SO3 at room temperature gives a mixture of
5-nitro-and
8-nitroquinolines
isoquinoline reacts with fuming nitric acid in concentrated (conc.) sul-
furic acid containing SO3 at 0°C to
give a mixture of
5- and 8-nitroisoquinolines.
Sulfonation of quinoline with oleum at 92°C gives mainly
quinoline-8-sulfonic acid
Sulfonation of isoquinoline with oleum at 92°C gives mainly
isoquinoline-5-sulfonic acid.
Alkyl and acyl halides react directly with the basic nitrogen atom of both the
compounds to give
quaternary salts.
with acetyl nitrate at 20°C, quinoline undergoes an addition-substitution reaction to give
3-nitroquinoline
The C P N bond of the pyridine ring in both of these compounds under goes nucleophilic addition at low temperature with “KNH2”, and the adduct on (oxidation) with “KMnO4” at low temperature gives
2-aminoquinoline and 1-aminoisoquinoline in a Chichibabin-type reaction.
Glycerol is dehydrated by sulfuric acid to
acrolein
Aniline undergoes a Michael-type addition with acrolein in an acid-promoted reaction to form
b-anilinopropanal
anilinopropanal undergoes an acid-catalysed cyclization to give
1,2-dihydroquinoline
Nitrobenzene aromatizes 1,2-dihydroquinoline compound to _________ and itself is reduced to_________
quinoline
aniline
_________moderates this last
exothermic step.
Ferrous sulfate
Indole ring occurs widely in nature as
alkaloids
the aromatic stability
of the benzene ring, the most important contributing structure of indole to its reso-
nance hybrid is its
enamine form
Because of the higher electron density in the heteroring, indole undergoes electrophilic substitution at _____in the pyrrole ring
C-2
Because of the higher electron density in the heteroring, indole undergoes elec-
trophilic substitution at C-2 in the pyrrole ring and regioselectively at_____
C-3
indole easily undergoes protonation to give
indolenium
indole is sulfonated at C-3 with________
pyridinium–N-sulfonat
indole is brominated at C-3 with___________ at 0°C
bromine in pyridine
Br2, Py, 0 C
indole is acetylated at C-1 and C-3 to give diacetyl derivative with___________
acetic anhydride in acetic acid
Ac^2O, AcOH
indole is methylated at C-3 with__________ at 80°C
methyl iodide in DMF
MeI ,DMF ,80 C
indole is formylated at C-3 with
_____and_____ at 5°C followed by alkaline hydrolysis (Vilsmeier reac tion)مهم
POCl3, DMF
indole is amino methylated at C-3 with______ and______ (Mannich reaction).مهم
HCHO, amines
(HCHO, HNR2)
